CA2644467C - Alpha crystalline form of perindopril arginine salt, its preparation process, and the pharmaceutical compositions that contain it - Google Patents
Alpha crystalline form of perindopril arginine salt, its preparation process, and the pharmaceutical compositions that contain it Download PDFInfo
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- CA2644467C CA2644467C CA2644467A CA2644467A CA2644467C CA 2644467 C CA2644467 C CA 2644467C CA 2644467 A CA2644467 A CA 2644467A CA 2644467 A CA2644467 A CA 2644467A CA 2644467 C CA2644467 C CA 2644467C
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Abstract
Description
FORME CRISTALLINE ALPHA DU SEL D'ARGININE DU PERINDOPRIL, SON PROCÉDÉ DE PRÉPARATION, ET LES COMPOSITIONS PHARMACEUTIQUES QUI LA CONTIENNENT
La présente invention concerne la forme cristalline a du sel de L-arginine du perindopril de formule (1) :
H
C02H ~
C (s) NH2 NH
(s) CO2Et son procédé de préparation ainsi que les compositions pharmaceutiques qui la contiennent.
Le perindopril, ainsi que ses sels pharmaceutiquement acceptables, et plus particulièrement son sel d'arginine, possèdent des propriétés pharmacologiques intéressantes.
Leur principale propriété est d'inhiber l'enzyme de conversion de l'angiotensine I (ou kininase Il), ce qui permet d'une part d'empêcher la transformation du décapeptide angiotensine I en octapeptide angiotensine II (vasoconstricteur), et d'autre part de prévenir la dégradation de la bradykinine (vasodilatateur) en peptide inactif.
Ces deux actions contribuent aux effets bénéfiques du perindopril dans les maladies cardiovasculaires, tout particulièrement l'hypertension artérielle et l'insuffisance cardiaque.
Le perindopril, sa préparation et son utilisation en thérapeutique ont été
décrits dans le brevet européen BP 0 049 658.
Le sel d'arginine du perindopril a été décrit dans le brevet européen EP 1 354 873. ALPHA CRYSTALLINE FORM OF PERINOPRIL ARGININE SALT, ITS PREPARATION METHOD, AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING IT
The present invention relates to the crystalline form α of the L-arginine salt of perindopril of formula (1):
H
C02H ~
C (s) NH2 NH
(S) CO2Et its preparation process as well as the pharmaceutical compositions which contain.
Perindopril, as well as its pharmaceutically acceptable salts, and more particularly its arginine salt, possess interesting pharmacological properties.
Their main property is to inhibit the conversion enzyme of angiotensin I (or kininase II), which allows on the one hand to prevent the transformation of the decapeptide angiotensin I to octapeptide angiotensin II (vasoconstrictor), and other to prevent the degradation of the bradykinin (vasodilator) into an inactive peptide.
These two actions contribute to the beneficial effects of perindopril in diseases cardiovascular diseases, especially high blood pressure and heart failure.
Perindopril, its preparation and its use in therapeutics have been described in European patent BP 0 049 658.
The arginine salt of perindopril has been described in European Patent EP 1,354 873.
-2-Compte tenu de l'intérêt pharmaceutique de ce composé, il était primordial de l'obtenir avec une excellente stabilité, principalement en termes d'hygroscopicité, de processabilité
de la poudre, de filtrabilité du solide, de broyage, de rétention de solvant.
L'obtention d'une forme cristalline bien définie permet de répondre à ce cahier des charges.
Le brevet EP 1 354 873 décrit le sel d'arginine du perindopril. Cependant, ce document ne précise pas les conditions d'obtention de ce sel sous une forme cristalline bien définie.
La demanderesse a présentement trouvé que le sel d'arginine du perindopril pouvait être obtenu sous une forme cristalline bien définie, présentant de ce fait des caractéristiques intéressantes de filtration, de séchage et de facilité de formulation.
Plus spécifiquement, la présente invention concerne la forme cristalline a du composé de formule (I), caractérisée par les pics de diffraction RX sur poudre suivants, mesurés sur un diffractomètre à anticathode de cuivre et exprimés en termes d'angle 2-thêta ( ) : 4,5, 7,9 et 13,5.
De façon préférentielle, la présente invention concerne la forme cristalline a du composé
de formule (I), caractérisée par les pics de diffraction RX sur poudre suivants, mesurés sur un diffractomètre à anticathode de cuivre et exprimés en termes d'angle 2-thêta ( ) : 4,5, 7,9, 13,5, 17,5 et 20,6.
De façon encore plus préférentielle, la présente invention concerne la forme cristalline a du composé de formule (I), caractérisée par le diagramme de diffraction X sur poudre suivant, mesuré sur un diffractomètre (anticathode de cuivre) et exprimé en termes de distance inter-réticulaire d, d'angle de Bragg 2 thêta, d'intensité et d'intensité relative (exprimée en pourcentage par rapport à la raie la plus intense) :
Distance inter- intensité relative Angle 2 thêta ( ) Intensité
réticulaire d Å
4,52 19,53 2211 88,7 7,94 11,12 2080 83,5 12,152 7,277 682 27,4 -2-Given the pharmaceutical interest of this compound, it was essential to get with excellent stability, mainly in terms of hygroscopicity, processability powder, filterability of the solid, grinding, solvent retention.
Obtaining a well-defined crystalline form makes it possible to respond to this Specifications.
EP 1 354 873 describes the arginine salt of perindopril. However, this document does not specify the conditions for obtaining this salt in a crystalline form well defined.
The Applicant has currently found that the arginine salt of perindopril could be obtained in a well-defined crystalline form, thereby presenting characteristics interesting filtration, drying and ease of formulation.
More specifically, the present invention relates to the crystalline form composed of formula (I), characterized by the following powder X-ray diffraction peaks, measured on a anticathode diffractometer and expressed in terms of 2-theta angle ( ): 4.5, 7.9 and 13.5.
Preferably, the present invention relates to the crystalline form a of the compound of formula (I), characterized by the X-ray powder diffraction peaks following, measured on an anticathode diffractometer of copper and expressed in terms of angle 2-theta (): 4.5, 7.9, 13.5, 17.5 and 20.6.
Even more preferably, the present invention relates to the shape crystalline of the compound of formula (I), characterized by the X-ray diffraction pattern powder following, measured on a diffractometer (copper anticathode) and expressed in terms of inter-reticular distance d, Bragg angle 2 theta, intensity and relative intensity (expressed as a percentage of the most intense line):
Relative inter-intensity distance Angle 2 theta () Intensity reticular 4.52 19.53 2211 88.7 7.94 11.12 2080 83.5 12,152 7,277 682 27.4
-3-Angle 2 thêta ( ) Distance inter- Intensité Intensité relative réticulaire d O (%o) 13,480 6,563 2492 100,0 14,029 6,308 422 16,9 14,948 5,922 552 22,1 15,873 5,579 493 19,8 17,531 5,055 1600 64,2 18,787 4,719 363 14,5 19,579 4,530 1078 43,3 20,635 4,301 1794 72,0 22,616 3,928 798 32,0 23,367 3,804 473 19,0 23,807 3,735 362 14,5 24,434 3,640 409 16,4 27,148 3,282 450 18,1 28,214 3,160 417 16,7 L'invention s'étend également au procédé de préparation de la forme cristalline a du composé de formule (I), dans lequel le perindopril est mis en solution dans l'eau avec de la L-arginine, puis un solvant apolaire et un solvant polaire sont ajoutés, et les cristaux obtenus sont filtrés, lavés puis séchés.
Parmi les solvants apolaires, on peut citer à titre d'exemple le méthylcyclohexane, le cyclohexane et le toluène.
Parmi les solvants polaires, on peut citer à titre d'exemple le diméthylsulfoxyde, la N,N-diméthylformamide, le N,N-diméthylacétamide et la N-méthyl-2-pyrrolidinone.
Les cristaux ainsi obtenus se présentent sous une forme compacte, constituée de baguettes.
Selon un mode de réalisation de l'invention, le perindopril est mis en solution dans l'eau avec de la L-arginine, puis du méthylcyclohexane et du diméthylsulfoxyde sont ajoutés, et les cristaux obtenus sont filtrés, lavés puis séchés.
L'invention s'étend aussi aux compositions pharmaceutiques renfermant comme principe actif la forme cristalline a du composé de formule (I) avec un ou plusieurs excipients inertes, non toxiques et appropriés. Parmi les compositions pharmaceutiques selon -3-Angle 2 theta () Interval Distance Intensity Relative Intensity reticular d O (% o) 13,480 6,563 2492 100.0 14,029 6,308 422 16.9 14.948 5.922 552 22.1 15,873 5,579 493 19.8 17,531 5,055 1,600 64.2 18,787 4,719 363 14.5 19,579 4,530 1078 43.3 20.635 4.301 1794 72.0 22.616 3.928 798 32.0 23,367 3,804 473 19.0 23,807 3,735 362 14.5 24,434 3,640 409 16.4 27,148 3,282 450 18.1 28,214 3,160 417 16.7 The invention also extends to the process of preparing the form crystalline has compound of formula (I), wherein the perindopril is dissolved in water with L-arginine, then an apolar solvent and a polar solvent are added, and the crystals obtained are filtered, washed and dried.
Among the apolar solvents, mention may be made by way of example methylcyclohexane, the cyclohexane and toluene.
Among the polar solvents, mention may be made by way of example dimethylsulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide and N-methyl-2-pyrrolidinone.
The crystals thus obtained are in a compact form, consisting of chopsticks.
According to one embodiment of the invention, perindopril is solution in the water with L-arginine, then methylcyclohexane and dimethylsulfoxide are added, and the crystals obtained are filtered, washed and then dried.
The invention also extends to pharmaceutical compositions containing as principle active the crystalline form a of the compound of formula (I) with one or more excipients inert, non-toxic and appropriate. Among the pharmaceutical compositions according to
-4-l'invention, on pourra citer plus particulièrement celles qui conviennent pour l'administration orale, parentérale (intraveineuse ou sous-cutanée), nasale, les comprimés simples ou dragéifiés, les comprimés sublinguaux, les gélules, les tablettes, les suppositoires, les crèmes, les pommades, les gels dermiques, les préparations injectables, les suspensions buvables.
La posologie utile est adaptable selon la nature et la sévérité de l'affection, la voie d'administration ainsi que l'âge et le poids du patient. Cette posologie varie de 1 à 500 mg par jour en une ou plusieurs prises.
Les compositions pharmaceutiques selon l'invention peuvent également contenir un diurétique comme l'indapamide.
Les compositions pharmaceutiques selon l'invention peuvent être utilisées pour inhiber l'enzyme de conversion de l'angiotensine I.
Les compositions pharmaceutiques selon l'invention peuvent être utilisées pour le traitement des maladies cardiovasculaires.
Un aspect vise également l'utilisation d'un composé de l'invention pour la fabrication de médicaments inhibiteurs de l'enzyme de conversion de l'angiotensine I.
Un aspect vise également l'utilisation d'un composé de l'invention pour la fabrication de médicaments destinés au traitement des maladies cardiovasculaires.
Les exemples suivants illustrent l'invention.
Le spectre de diffraction X sur poudre a été mesuré avec les conditions expérimentales suivantes :
-4a-Diffractomètre Siemens D5005 ; détecteur à scintillations ;
Anticathode cuivre, voltage 40KV, intensité 30mA ;
Montage 0 - 0, échantillon fixe ;
Température : ambiante ;
Domaine de mesures : 3 à 30 ;
Incrémentation entre chaque mesure : 0,04 ;
Temps de mesure par pas : 4s ;
Fentes fixes : 1,6mm ;
Filtre M (Ni) ;
Pas de référence interne ;
Procédure de zéro avec les fentes Siemens ;
Données expérimentales traitées avec le logiciel EVA (version 9.0).
EXEMPLE 1 : Forme cristalline a du sel d'arginine du perindopril -4-the invention, more particularly those which are suitable for oral, parenteral (intravenous or subcutaneous), nasal, tablets simple or sugar-coated, sublingual tablets, capsules, lozenges, the suppositories, creams, ointments, dermal gels, preparations injectables, drinkable suspensions.
The useful dosage is adaptable according to the nature and severity of affection, the way administration and the age and weight of the patient. This dosage varies from 1 to 500 mg per day in one or more takes.
The pharmaceutical compositions according to the invention may also contain a diuretic like indapamide.
The pharmaceutical compositions according to the invention can be used to inhibit the angiotensin I converting enzyme The pharmaceutical compositions according to the invention can be used to the treatment cardiovascular diseases.
One aspect also relates to the use of a compound of the invention for the manufacture of Angiotensin I converting enzyme inhibitors One aspect also relates to the use of a compound of the invention for the manufacture of medicines for the treatment of cardiovascular diseases.
The following examples illustrate the invention.
X-ray powder diffraction spectrum was measured with the conditions experimental following:
-4?
Siemens D5005 diffractometer; scintillation detector;
Copper anticathode, voltage 40KV, intensity 30mA;
Mounting 0 - 0, fixed sample;
Ambient temperature ;
Measurement range: 3 to 30;
Increment between each measurement: 0.04;
Measurement time in steps: 4s;
Fixed slots: 1,6mm;
M filter (Ni);
No internal reference;
Zero procedure with Siemens slots;
Experimental data processed with EVA software (version 9.0).
EXAMPLE 1 Crystalline form a arginine salt of perindopril
-5-Dans un réacteur sont introduits, à température ambiante et sous agitation, 1,5 kg d'eau, 328 g de perindopril et 155 g de L-arginine. Lorsqu'une solution limpide est obtenue, 630 g de méthylcyclohexane sont ajoutés, puis 4,7 kg de diméthylsulfoxyde sont additionnés lentement. Le milieu est ensuite laissé sous agitation jusqu'à ce que la température du mélange hétérogène se stabilise autour de 20,O C, puis le mélange est filtré, et le solide obtenu est lavé et séché.
Les cristaux ainsi obtenus se présentent sous une forme compacte, constituée de baguettes.
La teneur en eau du produit obtenu est d'environ 3,2%, ce qui correspond à un monohydrate.
Diagramme de diffraction X sur poudre Le profil de diffraction des rayons X de la poudre (angles de diffraction) de la forme a du sel d'arginine du perindopril est donné par les raies significatives rassemblées dans le tableau suivant, avec l'intensité et l'intensité relative (exprimée en pourcentage par rapport à la raie la plus intense).
Angle 2 thêta Distance inter- Intensité Intensité relative ( ) réticulaire d O ( ,fo) 4,52 19,53 2211 88,7 7,94 11,12 2080 83,5 12,152 7,277 682 27,4 13,480 6,563 2492 100,0 14,029 6,308 422 16,9 14,948 5,922 552 22,1 15,873 5,579 493 19,8 17,531 5,055 1600 64,2 18,787 4,719 363 14,5 19,579 4,530 1078 43,3 20,635 4,301 1794 72,0 22,616 3,928 798 32,0 23,367 3,804 473 19,0 23,807 3,735 362 14,5 24,434 3,640 409 16,4 27,148 3,282 450 18,1 -5-In a reactor are introduced, at room temperature and with stirring, 1.5 kg of water, 328 g of perindopril and 155 g of L-arginine. When a clear solution is obtained, 630 g of methylcyclohexane are added, then 4.7 kg of dimethylsulfoxide are added added slowly. The medium is then left stirring until the temperature of heterogeneous mixture stabilizes around 20, OC, then the mixture is filtered, and the solid obtained is washed and dried.
The crystals thus obtained are in a compact form, consisting of chopsticks.
The water content of the product obtained is approximately 3.2%, which corresponds to a monohydrate.
X-ray powder diffraction pattern The X-ray diffraction profile of the powder (diffraction angles) of the form has arginine salt of perindopril is given by significant lines gathered in the following table, with the intensity and relative intensity (expressed in percentage compared at the most intense line).
Angle 2 theta Inter-distance Intensity Relative intensity () reticular of O (, fo) 4.52 19.53 2211 88.7 7.94 11.12 2080 83.5 12,152 7,277 682 27.4 13,480 6,563 2492 100.0 14,029 6,308 422 16.9 14.948 5.922 552 22.1 15,873 5,579 493 19.8 17,531 5,055 1,600 64.2 18,787 4,719 363 14.5 19,579 4,530 1078 43.3 20.635 4.301 1794 72.0 22.616 3.928 798 32.0 23,367 3,804 473 19.0 23,807 3,735 362 14.5 24,434 3,640 409 16.4 27,148 3,282 450 18.1
-6-Distance inter- Intensité relative Angle 2 thêta ( ) Intensité
réticulaire d (A) (%) 28,214 3,160 417 16,7 EXEMPLE 2 : Composition pharmaceutique Formule de préparation pour 1000 comprimés dosés à 4 mg :
Composé de l'exemple 1 ...............................................................................
....... 4 g Hydroxypropylcellulose ...............................................................................
...... 2 g Amidon de blé
...............................................................................
.................... log Lactose ...............................................................................
...............................100 g Stéarate de magnésium ...............................................................................
........ 3 g Talc ...............................................................................
...................................... 3 g -6-Inter distance Relative intensity Angle 2 theta () Intensity reticular d (A) (%) 28,214 3,160 417 16.7 EXAMPLE 2 Pharmaceutical Composition Preparation formula for 1000 tablets dosed at 4 mg:
Composed of Example 1 .................................................. .............................
....... 4 g hydroxypropyl .................................................. .............................
...... 2 g Wheat starch .................................................. .............................
.................... log Lactose .................................................. .............................
............................... 100 g Magnesium stearate .................................................. .............................
........ 3 g Talc .................................................. .............................
...................................... 3 g
Claims (14)
caractérisée par les pics de diffraction RX sur poudre suivants, mesurés sur un diffractomètre à anticathode de cuivre et exprimés en termes d'angle de Bragg 1. Crystalline form of L-arginine salt of perindopril, of formula (I):
characterized by the following RX powder diffraction peaks, measured on a copper anticathode diffractometer and expressed in terms of Bragg angle
4,5, 7,9 et 13,5.
2. Forme cristalline a du composé de formule (I) selon la revendication 1, caractérisée par les pics de diffraction RX sur poudre suivants, mesurés sur un diffractomètre à
anticathode de cuivre et exprimés en termes d'angle de Bragg 2-thêta (~) :
4,5, 7,9, 13,5, 17,5 et 20,6. 2-theta (~):
4.5, 7.9 and 13.5.
2. Crystalline form a of the compound of formula (I) according to claim 1, characterized by the following powder X-ray diffraction peaks, measured on a diffractometer at copper anticathode and expressed in terms of Bragg 2-theta angle (~):
4.5, 7.9, 13.5, 17.5 and 20.6.
la raie la plus intense :
3. Crystalline form a of the compound of formula (I) according to claim 1, characterized by the following X-ray powder diffraction pattern, measured on a diffractometer, copper anticathode, and expressed in terms of inter-reticular distances d, angle of Bragg 2 theta, intensity and relative intensity, expressed as a percentage compared to the most intense line:
10, destinée à inhiber l'enzyme de conversion de l'angiotensine I. 13. Pharmaceutical composition according to any one of claims 8 to intended to inhibit the angiotensin I converting enzyme.
10, destiné au traitement des maladies cardiovasculaires. 14. Pharmaceutical composition according to any one of claims 8 to for the treatment of cardiovascular diseases.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0601748A FR2897866B1 (en) | 2006-02-28 | 2006-02-28 | ALPHA CRYSTALLINE FORM OF PERINOPRIL ARGININE SALT, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR06/01748 | 2006-02-28 | ||
| PCT/FR2007/000335 WO2007099217A1 (en) | 2006-02-28 | 2007-02-26 | α CRYSTALLINE FORM OF THE ARGININE SALT OF PERINDOPRIL, PROCESS FOR PREPARING IT, AND PHARMACEUTICAL COMPOSITIONS COMPRISING IT |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2644467A1 CA2644467A1 (en) | 2007-09-07 |
| CA2644467C true CA2644467C (en) | 2011-07-26 |
Family
ID=37022969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2644467A Expired - Fee Related CA2644467C (en) | 2006-02-28 | 2007-02-26 | Alpha crystalline form of perindopril arginine salt, its preparation process, and the pharmaceutical compositions that contain it |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US7846961B2 (en) |
| EP (1) | EP1989182B1 (en) |
| JP (1) | JP5255454B2 (en) |
| KR (2) | KR20120001818A (en) |
| CN (1) | CN101389603B (en) |
| AU (1) | AU2007220435B2 (en) |
| BR (1) | BRPI0708278B8 (en) |
| CA (1) | CA2644467C (en) |
| CY (1) | CY1117753T1 (en) |
| DK (1) | DK1989182T3 (en) |
| EA (1) | EA014716B1 (en) |
| ES (1) | ES2581982T3 (en) |
| FR (1) | FR2897866B1 (en) |
| GE (1) | GEP20125433B (en) |
| HK (1) | HK1129669A1 (en) |
| HR (1) | HRP20160644T1 (en) |
| HU (1) | HUE027898T2 (en) |
| MA (1) | MA30276B1 (en) |
| ME (1) | ME02456B (en) |
| MY (1) | MY151035A (en) |
| NO (1) | NO20083535L (en) |
| NZ (1) | NZ570367A (en) |
| PL (1) | PL1989182T3 (en) |
| RS (1) | RS54754B1 (en) |
| SI (1) | SI1989182T1 (en) |
| UA (1) | UA89905C2 (en) |
| WO (1) | WO2007099217A1 (en) |
| ZA (1) | ZA200807024B (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2318365E (en) * | 2008-06-24 | 2015-11-25 | Mylan Lab Ltd | Novel polymorphic forms of perindopril (l)-arginine and process for the preparation thereof |
| AU2009212902A1 (en) | 2008-09-03 | 2010-03-18 | Apotex Pharmachem Inc. | Amorphous form of an L-arginine salt of perindopril and processes of preparation thereof |
| SI23149A (en) | 2009-09-21 | 2011-03-31 | Silverstone Pharma | New benzatin salts of ace inhibitors, procedure for their preparationand their application for treatment of cardiovascular diseases |
| FR2985511B1 (en) * | 2012-01-05 | 2014-01-03 | Servier Lab | CRYSTALLINE DELTA FORM OF PERINOPRIL ARGININE SALT, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR2985512B1 (en) * | 2012-01-05 | 2014-06-20 | Servier Lab | PROCESS FOR THE PREPARATION OF L-ARGININE SALT OF PERINDOPRIL |
| CN103172696B (en) * | 2012-12-19 | 2014-12-17 | 宁波美诺华药业股份有限公司 | Preparation method of perindopril arginine salt of gamma-crystal form |
| FR3050380B1 (en) | 2016-04-20 | 2020-07-10 | Les Laboratoires Servier | PHARMACEUTICAL COMPOSITION COMPRISING A BETA-BLOCKER, A CONVERSION ENZYME INHIBITOR AND AN ANTIHYPERTENSOR OR NSAID. |
| EP3842035A1 (en) | 2019-12-23 | 2021-06-30 | KRKA, d.d., Novo mesto | Composition for the preparation of perindopril arginine granules, a method for their preparation and pharmaceutical composition comprising the granules |
| SI26268A (en) | 2021-11-18 | 2023-05-31 | Zupet Rok | Procedure for the preparation of the hydrated form of perindopril L-arginine |
| CN114149357A (en) * | 2021-12-29 | 2022-03-08 | 江苏嘉逸医药有限公司 | Preparation method of gamma-crystal form perindopril arginine salt |
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| FR2503155A2 (en) * | 1980-10-02 | 1982-10-08 | Science Union & Cie | NOVEL SUBSTITUTED IMINO DIACIDES, PROCESSES FOR THEIR PREPARATION AND THEIR USE AS AN ENZYME INHIBITOR |
| FR2811320B1 (en) * | 2000-07-06 | 2002-08-23 | Adir | NOVEL ALPHA CRYSTALLINE FORM OF TERT-BUTYLAMINE SALT OF PERINDOPRIL, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR2811318B1 (en) * | 2000-07-06 | 2002-08-23 | Adir | NOVEL GAMMA CRYSTALLINE FORM OF TERT-BUTYLAMINE SALT OF PERINDOPRIL, PREPARATION METHOD THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR2811319B1 (en) * | 2000-07-06 | 2002-08-23 | Adir | NOVEL BETA CRYSTALLINE FORM OF TERT-BUTYLAMINE SALT OF PERINDOPRIL, ITS PREPARATION METHOD AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| FR2838648B1 (en) * | 2002-04-18 | 2004-05-21 | Servier Lab | NEW PERINDOPRIL SALT AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING IT |
| FR2897865B1 (en) | 2006-02-28 | 2008-04-18 | Servier Lab | BETA CRYSTALLINE SHAPE OF PERINOPRIL ARGININE SALT, PROCESS FOR PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME |
| PT2318365E (en) | 2008-06-24 | 2015-11-25 | Mylan Lab Ltd | Novel polymorphic forms of perindopril (l)-arginine and process for the preparation thereof |
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